I use coach.me - the automation is via their undocumented mobile APIs https://github.com/jmaddi/liftapp-client (Lift is coach.me's previous branding)

I like https://chains.cc/, though I'm not aware of any way to automate it.

Commit on iOS is a well made example.

OrgMode also handles this out of the box (or at least what you'd call out of the box on OrgMode...)

I use dontbreakthechain.com